285 Terwillinger Rd, Chesapeake, VA 23323
OFF MARKET

$496,500

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,960 sqft (on 0.41 acres)

285 Terwillinger Rd, Chesapeake, VA 23323

Deep Creek South
Est. Refi. Payment $2,903/mo*
Refinance Your Home
Currently Off Market - Sold May 7, 2020 for $332,900

Home Value

Trulia Estimate
$497K
Since last month
$200 (0%)
Since last year
Increased$23K (+4.7%)
Since last sale
Increased$163K (+49.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +83% in the last 10 years
MonthEstimated value
2026
August 2026$496K
July 2026$497K
June 2026$501K
May 2026$496K
April 2026$495K
March 2026$487K
February 2026$480K
January 2026$472K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
324 Mobile Dr, Chesapeake, VA
0.18
Single-Family Home
$436,550
04/07/26
3
2
1,675
2609 Mossgate Ct, Chesapeake, VA
0.39
Single-Family Home
$424,605
07/09/26
4
3
2,203
444 Fleming Cir, Chesapeake, VA
0.39
Single-Family Home
$464,000
07/09/26
4
3
2,100
510 Creekwood Dr, Chesapeake, VA
0.45
Single-Family Home
$535,000
01/16/26
4
2.5
1,948
2717 Derry Dr, Chesapeake, VA
0.46
Single-Family Home
$460,000
01/13/26
4
2.5
1,948
2317 Eagle Dr, Chesapeake, VA
0.50
Single-Family Home
$480,000
06/22/26
4
3
2,128
2808 Covey Ct, Chesapeake, VA
0.35
Single-Family Home
$435,000
04/03/26
4
2
1,682
532 Shelview Cir, Chesapeake, VA
0.33
Single-Family Home
$475,000
04/30/26
4
2.5
2,006
2709 Cedar Rd, Chesapeake, VA
0.39
Single-Family Home
$360,000
06/11/26
4
2
1,458
2152 Millville Rd, Chesapeake, VA
0.47
Single-Family Home
$471,500
11/21/25
4
2.5
2,200

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
2602 Cecilia Ter, Chesapeake, VA 23323
0.09
$850,000
6
4
3,500
For Sale
2505 Calonia Arch, Chesapeake, VA 23323
0.13
$489,900
3
2.5
2,000
Recently Sold
324 Mobile Dr, Chesapeake, VA 23323
0.18
$436,550
3
2
1,675
Recently Sold
228 Terwillinger Road, Chesapeake, VA 23323
0.18
$578,900
5
3.5
2,402
Off Market
2428 Annie Cir, Chesapeake, VA 23323
0.22
$551,000
5
2.5
2,384
Recently Sold
208 Terwillinger Rd, Chesapeake, VA 23323
0.24
$405,000
3
2
1,424
Recently Sold
705 Creekwood Dr, Chesapeake, VA 23323
0.27
$595,000
5
4
3,000
For Sale
709 Creekwood Dr, Chesapeake, VA 23323
0.27
$560,100
5
2.5
2,550
Off Market
629 Creekwood Dr, Chesapeake, VA 23323
0.27
$500,000
4
2.5
2,150
Recently Sold
718 Creekwood Dr, Chesapeake, VA 23323
0.28
$560,000
4
3
2,423
Recently Sold
2425 Annie Cir, Chesapeake, VA 23323
0.29
$513,700
4
2.5
2,701
Off Market
633 Creekwood Dr, Chesapeake, VA 23323
0.29
$555,000
3
2.5
2,034
Recently Sold

Local Information

  • Map ViewExplore the area around 285 Terwillinger Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Lot Size
0.41 acres
Living Area
1,960 sqft
Price/Sqft
$253
Parking
Garage

About this House

LOCATION! LOCATION! LOCATION! If you've always wanted to be in the Grassfield school district, then look no further. This gorgeous home with updated kitchen and baths is the perfect home for you. Shows the pride of Homeownership, well maintained home and waiting for its new owners. Just imagine sitting in your backyard entertaining while barbecuing on the grill. This home is near play area and centrally located to shopping and interstate.
285 Terwillinger Rd, Chesapeake, VA 23323 is a 4 bedroom, 3 bathroom, 1,960 sqft single-family home in Deep Creek South, built in 1999. It last sold for $332,900 on May 7, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $496,500, with a rent estimate of $2,826/month.

Home Details for 285 Terwillinger Rd

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Laminate
Interior Details
AtticNumber of Rooms: 7Types of Rooms: Walk In Closet, Breakfast Nook, Laundry Room, Master Bath, PantryCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylFoundation Type: SlabGardenLawnPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Garage Attached, Off Street, On Street

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.41 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
May 7, 2020
Source: N/A
Sold
$332,900
Mar 26, 2020
Source: Agent Provided
Listed For Sale
$332,900
Sep 5, 2000
Source: N/A
Sold
$147,000
Apr 14, 1999
Source: N/A
Sold
$133,000

Market trends in Deep Creek South

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$496K
Sale-to-List Price
—
Price per sq ft
$218
Available listings
48
7MoM

Around this home

Neighborhood Overview

Deep Creek South
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Deep Creek South

At least 81 Trulia users voted on each feature.

  • 98 % Say car is needed

  • 95 % Say yards are well-kept

  • 91 % Say it's dog friendly

  • 90 % Say parking is easy

  • 86 % Say there's holiday spirit

  • 80 % Say kids play outside

  • 77 % Say people would walk alone at night

  • 76 % Say it's quiet

  • 74 % Say there's wildlife

  • 65 % Say neighbors are friendly

  • 55 % Say they plan to stay for at least 5 years

  • 53 % Say streets are well-lit

  • 41 % Say there are community events

  • 35 % Say there are sidewalks

  • 26 % Say it's walkable to grocery stores

  • 13 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Sonya Cunningham
    "Low stress area. Convenient location. Could use more restaurants. Over all the schools are awesome and the community is supportive. "
    0
    Flag
  • Kaylermeg
    "Halloween is soo much fun! Everyone hangs out in their garages and makes it extra special for all of the kids with fun drinks and snacks, they usually have a DJ too! Usually there is a neighborhood bar crawl in the summer!"
    2
    Flag
  • Trulia User
    "I lived in this neighborhood for two years now. The Folks are very friendly. The neighborhood is very pet friendly and well suited for family."
    1
    Flag
  • Trulia User
    "great neighborhood and it is highly recommended. this is a great place to live and you will enjoy it. "
    0
    Flag
  • Trulia User
    "There is a nice long path running along the length of the dismal swamp that would be great for walking dogs. "
    2
    Flag
  • Trulia User
    "wonderful location to raise children. great schools and the best parks. love watching the boats go by. would recommend this area to anyone. "
    0
    Flag
  • Trulia User
    "great area! very family friendly and the best schools. I would recommend this area for big families. "
    0
    Flag
  • Cgraes
    "This is a safe, quiet, and a great place for families. The tolls and traffic are the downers. Very congested considering tons of communities connected to two main low capacity roads available."
    2
    Flag
  • Christy R.
    "Dogs are a welcomed part of this community, I always see people walking their dogs, but I never see any droppings!!! "
    3
    Flag
  • Leaosc
    "Large dog friendly community. Some owners don’t know how to pick up after their furry family members. That makes it frustrating."
    2
    Flag
  • Sayhelo
    "I love my neighbors, and the people who live here. Good schools, nice shops, clean here. I have many food stores to choose from and other shops. The only thing I don’t like is the tolls, and the large amount of gun shot I hear in this area, which I guess is for control of wild life in the area."
    6
    Flag
  • Ddaniels36
    "We have lived in this neighborhood for 20 years. My children grew to be smart and strong here, and they had many friends. The schools are great and the teachers are wonderful. The neighbors are kind and caring. Our jobs are taking us to another state, but we will always treasure the memories and friends we have made here in this safe and secure neighborhood."
    0
    Flag
  • Sheldongreg
    "People walk they’re Dogs regularly on a leash and pick up any waste as the dog leaves it. There’s a waste can especially for Dog Waste while on your walk with your Dog. It’s very pleasant in my neighborhood to walk the Dog."
    2
    Flag
  • Michael S. S. (.
    "Neighborhood park and community pool. Meetings and holiday gatherings, parties, festivals, hay rides, parades and night out activities keep this diverse community connected."
    1
    Flag
  • Sayhelo
    "There are many folks with dogs, horses. I have also seen people with Gooses,and one guy who walks his chickens around the neighborhood. Never a problem with people who complain about others animals."
    4
    Flag
  • Mary-elizabeth H.
    "We love our neighborhood. It’s quiet and clean. It has two playgrounds, a pond and plenty of walking trails. "
    2
    Flag
  • Sayhelo
    "They have a really nice school system, although the new bridge was built, the toll is a little Steep. We don’t have much shopping on this side of the bridge . We have a few food stores, Walmart, food loin, but we need a place that will offer fresh fruit, and vegetables. "
    0
    Flag
  • Sayhelo
    "Many new homes with small children. Great schools, close to shopping,tech college, A nice variety for eating out"
    0
    Flag
  • Megan m.
    "I have lived in the area for 10 years Have seen lots of wildlife Friendly neighbors And easy to get around"
    2
    Flag
  • Yunilda B.
    "Love this neighborhood. It’s peaceful, beautiful, friendly and good for raising kids. I wish has more restaurants around so we can have options for dining. "
    4
    Flag
  • Sasha_The_Great
    "Loveeeeee my community! It’s very friendly and quiet. They are always having fun community events at the pool and club house. You will love this sought after friendly neighborhood. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 285 Terwillinger Rd

  • What is 285 Terwillinger Rd estimated to be worth?
    Trulia's estimated value for 285 Terwillinger Rd in Chesapeake, VA is $496,500.
  • What is the price history for 285 Terwillinger Rd?
    285 Terwillinger Rd in Chesapeake, VA last sold for $332,900 in May 2020.
  • Is Chesapeake a buyer's or seller's market?
    Chesapeake is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Chesapeake?
    The median sale price in Chesapeake is $496K.
  • Does 285 Terwillinger Rd have air conditioning?
    Yes, 285 Terwillinger Rd in Chesapeake, VA has air conditioning.
  • Does 285 Terwillinger Rd have a pool?
    Yes, 285 Terwillinger Rd in Chesapeake, VA has a pool.

Explore by feature - Pet Friendly

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